


Wicked Game

by conanchristopher



Category: Conan (TV Show), Late Night Host RPF, Real Person Fiction, US Comedians RPF
Genre: 10s Conan, Angst, Enemies to Lovers, Explicit Language, Explicit Sexual Content, F/M, Office Sex, Rough Sex, Smut, Submission, beard Conan
Language: English
Status: In-Progress
Published: 2020-07-06
Updated: 2021-03-04
Packaged: 2021-03-04 22:54:23
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 15
Words: 14,725
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/25104253
Author URL: https://archiveofourown.org/users/conanchristopher/pseuds/conanchristopher
Summary: What a wicked thing to do, to let me dream of you.
Relationships: Conan O'Brien/OC, Conan O'Brien/Reader
Comments: 2
Kudos: 20





	1. Chapter 1

**Author's Note:**

> Hi folks, I'm back... and I brought something slightly different. I hope you enjoy it.

“God, I need a good fuck.”

Conan was against one night stands. He didn’t want to get involved with a woman, or a succession of women, who could ruin his career by leaking some story about the time they were together. But being a talk show host was lonely, despite what people thought. He traveled constantly, and talked to a lot of celebrities, but the preparation, rehearsal and the peculiarities of the job took most of his time. He had forgotten what a relationship was like at that point. The idea of being with someone was tempting, no matter who and how.

Conan was in his late forties, but that wasn’t a problem. He was attractive in his own way, well put together and he knew women would do anything to sleep with him; he was famous after all. But even with women showing interest by direct or indirect flirting, he didn’t seem to like any. Many of them were his employees, but Conan had a policy of not getting intimate with staff members. He had a lot of energy and no place to waste it.

To make things worse, Sona had taken a six month break, and he had no assistant. After a month, the weight of the job started to fall over his shoulders and he was pressed by Jeff Ross to get a temporary assistant. He assured Jeff he could take care of things himself, after all, his extra energy had to go somewhere else. Opposing Conan and thinking about the future of the show, Jeff called Sona and asked her for advice. Sona knew Conan very well, and suggested someone as tough as she was, to take the job.

Conan was sitting on his office with his legs over the desk, a bit after rehearsal, sporting his famous leather jacket, thinking if someone would catch him masturbating if he started at that exact moment. He could lock his door and just go on with it. It would be unusual, since he never does it, but he needed some sexual relief, or else, he would go insane. Good thing he didn’t start, because Jeff came in as he thought of it, which made Conan roll his eyes, because he knew what he was going to talk about.

“Conan, I called Sona today and we decided who’s gonna replace her while she’s gone.” The door behind Jeff was open, but Conan didn’t notice at first.

“I told you Jeff, I don’t need a fucking assistant. I can handle this on my own.” Conan was tired of discussing this issue, and the lack of sex made him a bit moody.

“Yeah… right. You think that we haven’t notice how tired you are? And yet, you still want to do this all by yourself.”

Conan looked away, annoyed by the discussion. He thought a new assistant was unnecessary, simply because he had additional people who could do stuff for him. He scratched his beard, thinking about the money that would be wasted on hiring someone new. He heard a whisper but didn’t bother to look back at Jeff. 

“Good morning, sir.” he heard a deep, sweet female voice say. He looked back at the door as Jeff introduced the one who would work for him for the next five months.

Conan didn’t bother to stand up. He looked at her, she was wearing a black dress and heels, with her arms crossed, standing next to Jeff. Her legs were long and beautiful, sculpted into perfection. She had long, wavy brown hair. They stared at each other for a few seconds until Jeff broke the silence. 

“This is Liliana Peregrín.” Jeff said, making reference to the gorgeous woman next to him. “She’s Sona’s friend. I hope you guys can get along.”

She came to shake his hand as a professional, even though he didn’t seem to care. She extended her arm at him, who was still sitting on his desk. As they shook hands, he looked at her, her caramel colored eyes were so warm and inviting… but he remained stoic at her sight. Her hand was as soft as hands could be. She smelled amazing. He felt like a horny teenager, thinking about all those things about a woman he didn’t know for more than two minutes.

She tried her best to seem friendly, but he had this very serious look in his blue eyes. This reception was colder than she expected. She had been watching his show for years and yet, she never thought she would see him in person with such an expression. Real life as it seemed, was very different from television.

“Sona told me you needed some help and you were too stubborn to ask for it.” She said. He looked away, as she took a few steps back. “She just forgot to mention how unpleasant you are.”

His head turned at her menacingly. He could’ve fired her because of that. Her thick Hispanic accent gave her a certain authority, she was confident and she didn’t seem to fear the look he gave her. Jeff was amused by all this, Sona was completely right. He left the room in silence and let them both know each other better.

“First of all, I don’t need you.” He began immediately, as Jeff shut the door.

“It’s not your call. Jeff won’t let you do anything.” She replied.

He stood up, finally. She noticed his long legs, as he walked to her, standing in the middle of his office. He was tall, a bit larger than she expected. He stopped right in front of her, a few inches of distance. She could smell his body, his deodorant. That delicious scent, all over his clothes. She remained indifferent, however.

“You know I could fire you this instant, right?” he said, in a low, threatening tone. 

She felt her skin tingle, but replied daringly. “So why don’t you, Conan?”

His heart was beating extremely fast. “Don’t play games with me, Liliana.”

He was baffled at the fact he couldn’t scare her, even trying his best. He cursed Sona in his head; she found one who’s hard to break, like she was herself. The girl turned and walked to the door, giving one last look at Conan.

“Do myself and yourself a favor. Call me Lily, like everybody else. My name sounds horrible in your accent.”

She closed the door, leaving a trail of her perfume in the air, and Conan stared at the doorknob for a couple of seconds.

She was really, really hot.


	2. Chapter 2

“Why didn’t you tell me he was an ass, Sona?” said Lily, holding her cellphone tight, with anger.

“He is… playfully.” Sona answered, feeling a bit guilty.

Sona also knew that by saying those things, she could scare Lily out of the job. She mentioned the stubbornness, but not the recent mood swings and his current behavior, and the fact he also opposed to have a new assistant. Sona got used to Conan’s peculiarities, but some things also needed an explanation she didn’t provide, for one simple reason: she didn’t trust anyone else to do it.

“Give me a good reason to keep doing this. It’s been one day and I already regret it.” Sona could hear Lily’s loud breathing through the phone. She was furious.

“Please, Lilita. Do it for me. He really needs help.”

She sighed. Sona could feel her frustration from the other side of the world. “Okay.”

“He lost a show recently.” Sona said. “We’ve been on tour for months now, and it finally ended… but give him time to heal. He’s not normally like this.”

“Why did you have to have a break right before he’s scheduled to come back?”

Sona sighed. “It’s just for a few months. I feel burnt out… the tour took most of my energy. You’ll be fine...”

Lily sighed. “Yeah, I suppose I will. May I call you for advice when I need it? He’s like a grumpy baby.”

“Of course you may.” Sona nodded. “Thank you, Lily. Thank you.”

Lily grunted as she turned off her cellphone. She was a freelance worker until Sona offered her this job. She was interviewed by Jeff himself, who seemed to like her and her spirit. She had prior experience working at different shows in the entertainment business, but never as a direct assistant to the host. She would be fine, she was good at problem solving and she knew Los Angeles pretty well, despite being a foreigner. Conan wasn’t having it, but Lily would prove her worth in time.

Meanwhile, Conan was stressed out about his comeback. The Tonight Show debacle affected him in various degrees, physically and mentally. The first day after losing his dream job, Conan looked at himself in the mirror and shrugged, thinking that he wasn’t contractually obligated to shave anymore. This thought grew into a beard, surprising even this crew. Conan had grown a beard before, during the writer’s strike. But that was different. His life changed, an event he never predicted happened. His appearance reflected on that.

Now, as he was coming back, over a new network and a different show name, he started to feel the pressure. With Sona on his side, everything was easier, but she needed to leave… and now he had Lily. He frowned at the thought of her and she was always around, of course. She was extremely good at her job, and as much as Conan tried to distance himself and show total lack of interest, she was… She defied him in a way he was never defied before. It felt unusual to him.

Conan thought about it, maybe the lack of sex was affecting him more than he noticed. As days went by, he tried as much as he could to keep everything professional, as he should. Her scent lingered over his stuff, at the office where she always was. He avoided her gaze, fearing he would be hypnotized one day. He felt his body getting closer and closer to her as she discussed remote locations, possible bits and props and talked about his calls. He was drawn to her, like he couldn’t escape her attraction; the desire to bang her against the wall, over his office desk, everything he wanted to do with her… couldn’t Jeff just fire her?

Conan knew he could fire her. Yes, he was the CEO. But nonetheless, he needed her help. She was really efficient at her job, she went around as silently as humanly possible, organizing his life like no one has ever done before. Conan joked around about Sona, and he loved her, but this girl was different. Sona was also excellent at her job, but Lily… he didn’t want Lily there. Conan must have left a bad taste on her mouth after the way he received her on her first day.

Lily wasn’t too keen of Conan either, after his initial reaction, she decided to keep her distance. His smell was all over the place, because he was all over the place. Entering his office gave her goosebumps. She wore heels on her first day, but decided to keep it casual afterwards like everybody did. He would tower over her while standing next to her, the fabric of his clothing emanating that delicious, manly smell of Old Spice he always had, like he had just showered. His whole office, even the couch. It all smelled like him. Unfortunately, the man didn’t seem too inviting.

Conan noticed her shift on clothing, she used to go from dresses to jeans and flannel shirts, red lipsticks and perfect makeup to no makeup at all, and he had to admit to himself it worked every time. When she didn’t have her hair straightened or in a pony tail, she had it in a bun, sometimes he felt like touching those incredibly soft curls of her hair, and he thought about it, daily. Her smell was confusing him. She was so young, but not at all naive, and he just decided not to look at her while they were working. She was so goddamn beautiful it was almost a distraction.

Lily’s thoughts of calling Sona eventually faded away, she could do this on her own. They barely spoke a word to each other, and during rehearsal, they tried not to look at one another. Both would frown when their eyes met, and the staff noticed how they absolutely hated each other. Conan just wanted an occasion for her to screw up badly so she could be fired and he would forget about her forever. And finally, after a few weeks, something happened.


	3. Chapter 3

Conan was about to enter the stage when he received the information that both of his guests for the day had canceled their appearances. Conan is usually cool when someone misses a show but this time, he had no backup guests. It wasn’t easy to contact them, people had other stuff to do. It wasn’t like ‘hey, Norm MacDonald! Get dressed and show up at studio fifteen on the Warner Bros. lot in ten minutes because we have a show.’

“God, oh my god where’s Lily?” Conan said, a bit loud.

Lily ran to Conan’s office. “I’m here, I’m here, I am aware...”

“You know we don’t have guests, don't you?” Conan was furiously buttoning his shirt up, his button shirt still not tucked and his undershirt visible.

“Yeah, I know, I’m taking care of it as we speak...” Lily said, without looking at him, what she usually did.

“I can’t have a show without fucking guests, maybe if you did you job like you’re supposed to, I wouldn’t...” he mumbled frowning at her. Before he could finish, she spoke.

“It’s not my fucking job to call guests, I’m not your booker and you know that.” Lily walked to him, saying it in a lower tone, showing him she wasn’t afraid.

“I’m doing my best” she continued “and it would mean a lot to me if you didn’t act like a fucking asshole.”

Conan was fuming, his face getting redder and redder. “This is how show business works, Liliana. Get used to it.”

“No it’s not!” she raised her voice. “I’ve worked for many people before and none of them was as insufferable as you!”

Conan stepped closer to Lily and she didn’t move, she also had a frown and they were looking at each other right in the eyes. Conan had baby blue eyes, the purest blue she had ever seen, now darkened by anger. He was breathing hard, out of rage, clenching his jaw. How could she be like this? Why was she there? She had her hands on her hips, and she didn’t seem to flinch at him. He had no way to intimidate her. He looked at her shoulder as the thin strap of her white blouse kept sliding down. She fixed it, and tuned away from him.

“Tom Hanks was in the lot and I talked to him personally.” Conan looked at her long legs as she bent to get her denim jacket out of his couch. “He agreed to cover up the two spots for you since he was one of your first guests on the Tonight Show.”

Conan sighed loudly, out of relief and frustration.

“You have five fucking minutes.” Lily said as she got out.

Conan swallowed as he saw her go, and prepared himself to go to the stage. He had to clear his head. He just wished her away… he wanted Sona back, at least they wouldn’t hate each other. He relaxed and did his job, as a professional, looking around at times to see if he could see Lily, but she wasn’t there. It was comforting, because she was probably pissed at him and seeing a pissed off person next to the audience would throw him off his rhythm. The interview with Tom Hanks went as planned, he was really kind about it, and he was willing to help Conan when he needed. Fortunately he was free and around to show up. Conan wrapped everything up and left the stage to change. He saw Andy on the way to his dressing room.

“Hey Conan, may I… talk to you?” Andy said.

“Sure.” Conan said as they walked together.

“Listen Conan, I don’t know what you have against Lily, but you should stop.”

“What do you mean?”

“You guys fight all the time, we all know that and the interns can hear it.” Andy seemed annoyed.

Conan sighed. “We don’t get along.”

“No, she’s very sweet. She can be a little bit too honest and opinionated, but she has a good heart. She worries about us.” Andy said.

“She’s so...”

“It’s like you’re putting your frustration all over her. She isn’t the one to blame.”

Conan grunted.

“You like her… don’t you?” Andy asked, almost certain of it.

Conan frowned. “No, I don’t.”

“Hm.”

“Let’s just go home okay, Andy?” Conan seemed annoyed at the question, which confirmed Andy’s suspicion.


	4. Chapter 4

The next day, Conan went to talk to Jeff about Lily. She screwed up. But no, Jeff was levelheaded and he knew that Lily actually saved the day. His guests did apologize and rescheduled their respective interviews. Conan’s staff and people who came in to work indirectly for him seemed to like her enough and Jeff knew how important this was. Conan was hoping Sona would come back soon, but the days felt longer and he felt more pissed every singe day he had to deal with Lily on his office. He had to swallow his pride, his producer was advising him, they worked together since the Late Night years… he knew what was best for the show.

Lily kept wondering what she did to Conan  to  be treated like that. Maybe he just missed Sona the way she was, but Lily was doing her best. Not even talking less and not looking at him made the situation better. She tried to better her facial expression as she looked at him, but he was always grumpy when looking at her. Yes yes, he was the boss, and she couldn’t do anything about it. She regretted taking the job sometimes, but the pay was good, and Sona was a great friend and Lily felt she had to help. But this job certainly shattered any hope she had of show business being decent to have a career in. It was one of the reasons why she was freelancing before this.

The situation kept escalating to the point of interns being scared of the interactions of the two. One day, Conan came back from shooting a remote, stopped to talk to his prop master Bill Tull, before walking to his office. He was wearing his classic brown leather jacket with skinny jeans as he used to, when filming outside. He took maybe five to ten minutes to go back and he caught Lily talking to Sona on the phone. She was a bit loud and he could hear her before entering the office. He stopped outside to listen to what she had to say.

“Guy’s a dick, Sona. There’s nothing I can do to work it out.”

There was a silence as Sona spoke. Conan couldn’t hear her. Lily sighed. “Of course. I tried. He won’t even look at me.”

Conan opened the door slowly and noticed Lily was reading something work-related. She wasn’t paying attention to the door.

“Yes, yes, I know. But he keeps frowning at me like I’m the one to blame for his problems.”

Silence again, Sona was speaking. “I don’t know why! Whatever it is, I would help. I hate being treated like garbage.”

Conan listened to it, and he knew deep inside, it was true. A little before he entered, Lily finally said.

“He needs to get laid.”

“You don’t have anything to do with my life.” Conan said, stepping in immediately after Lily closed her mouth.

“I’m sorry.” Lily said.

“Do you think it’s easy to manage an entire team and hosting a show after mine was taken from me the last time?” He furiously closed the door behind him. 

Lily frowned. “Maybe if you stopped blaming me for your problems that I didn’t cause, we could get along.”

“If you weren’t so stubborn and petty maybe I could stand you.” Conan fired back.

Lily stood up. She was wearing a blue blouse and tight jeans with sneakers, since they just got back from a shooting and they had to walk for a bit. “Listen, Conan. We can make things right, but it’s not only on me.”

“The thing is, I don’t want to work with you Lily. It’s impossible.”

She got close to him. “It’s impossible because you’re making it impossible.”

Conan grunted.

“What do I do to make you so angry?”

“Well, speculating about my private life isn’t a good thing.” He frowned at her. “I wonder what else you say to people behind my back.”

“I don’t say it behind your back, you moron. I’ll say it to your face. You’re a dick.”

She walked to the door to leave and Conan got out of the way.

“You just didn’t fucking say that.” he said as he turned to her.

She stopped, her hand on the doorknob, and turned to him.

“Yes, I did!” she snapped, pointing her finger at his chest. “You are a privileged, spoiled child and I wonder why you have friends!” 

Conan moved closer, her back was now pressed to the door. They stared at each other. “You’re an awful human being, you know that?”

Her lower lip quivered. “You’re worse.”

She kissed him, the sexual tension between the two was so great it could be felt like a wave. He immediately accepted her soft, warm lips. He held her close, her back firmly pressed against the door as he sucked her face off, like he never did to other woman before. She wrapped her legs around his waist as she grabbed his hair with one hand and his shoulder with the other. He moaned softly against her mouth, now placing his free hand under her blouse and feeling her breasts underneath.

He slowly moved her to the couch, none of them giving any signs that they wanted to stop at any moment. Their mouths only separated from each other to breathe. She took control and sat him on the couch. She moved on top of him and she could feel his cock getting harder and harder as she kissed him. He held her close as she rubbed her crotch against his, feeling his boner and longing for it. As she was undoing his belt, there was a knock on the door.

“Conan? It’s Mike.”

Both of them stopped kissing and looked at each other with wide eyes. Their heavy breathing was quickly covered by Lily’s hand, she covered his mouth and her own. Mike continued calling.

“Conan?” Mike called again. He twisted the doorknob to open the door before he was interrupted:

“I don’t think he is inside.” Andy said. “I saw him talking to Bill Tull a few minutes ago.”

“Oh, thanks Andy.”

Mike left, and Lily and Conan relaxed. They still looked at each other for a few seconds, like they saw death, but she quickly got up and sat next to him. He put his hands over his face still breathing hard, for the making out and the scare. Lily was also breathing hard, looking at him. H is face was red,  and he was  sweating a bit. Lily looked down to him and immediately looked away. He still had a massive boner and maybe it wasn’t the right time to talk about it. Silence invaded the room, when he finally spoke.

“So, did you get my stuff from the laundry?”


	5. Chapter 5

Conan and Lily continued not looking at each other, but now because the sexual tension was unbearable. He was a great kisser, his big hands were warm and he knew where to place them, he smelled great and his lips were extremely soft… Lily couldn’t just forget that. Damn, he was a looker. She was on her late twenties by now, and she had never desired an older man before, but that changed the minute they locked lips. She couldn’t stop thinking about it. All Lily could imagine now is Sona laughing at it, she always talked about how unattractive Conan was. They were great friends, like brothers, but Sona would never sleep with him, even if her life depended on it.

Conan felt like an idiot, now realizing he couldn’t hold his attraction back any longer. It was really difficult seeing her reading his schedule and not think about that day on the couch and how they would’ve gone all the way if Mike hadn’t interrupted. It was extremely wrong, this was office space, but her lips were so close… he couldn’t justify it to anyone. He wouldn’t be fired of his own company of course, but he was known by his great work ethic and he wouldn’t let it be destroyed by having sex with his assistant on the couch. She was Sona’s friend, what was he thinking? This couldn’t happen, it couldn’t…

“Ready?” Lily asked, bringing Conan back to planet Earth.

“Ready, I guess.” Conan said. Lily noticed he seemed nervous, and she was trying to make him feel better.

“Are you worried about something?” She asked.

“I’m fine, Liliana.” he sighed, and she noticed a bit of annoyance in his voice.

She rolled her eyes. “Okay. I’ll be here if you want to insult someone.”

Lily was wearing a very nice baby pink dress. It was hot outside, of course. Los Angeles. But why did she have to wear a dress? But not the other women, no… just her. Her legs were amazing. Her exposed shoulders. That’s why he tried not to look. Lily observed him. He was wearing a darker blue suit and a black tie with a white shirt. It was the way he dressed himself every day to host, but somehow… after their little encounter he looked more and more attractive every time she looked at him.

“You’re being dramatic.” He turned to her.

“Oh yes, it’s always my fault, isn’t it?” she fired at him.

He frowned at her. “You just need someone to put you in your place, at least once.”

Conan didn’t know if the suggestion was snarky or mildly sexual. “I think you’re the one who could use some discipline.”

She laughed out loud. “Yeah, right. Just go and do your comedy thingy, old man.”

She sat on the couch and he followed. She had her legs crossed and she looked at him as he kneeled. She was giggling at him, but let him made his move. He uncrossed her legs and opened them, sliding his big, warm hands up her thighs and under the fabric of her dress. He brought her hips closer and looked at her in the eyes. Her smile faded away, replaced by a mix of surprise and attraction.

“I still have twenty minutes.”

Her mouth was still wide open as Conan took her panties off, down her ankles. She got rid of her panties, sliding her down with her feet, so she could open her legs. He brought his head closer to eat her up, something that he thought about constantly. Yeah, she was right. He needed sex. Sex with her would be his first choice. He tasted her, so warm and pretty wet for someone who pretended she wasn’t at all attracted to him. Her hands went to his hair as he sucked her lips and played with his tongue, licking her. She started to sigh and moan as his hands went up to her, feeling her stomach and her breasts. Conan himself was moaning against her, and the taste of her invading his mouth.

Lily’s hands went down to his hair, tugging it, guiding it to the right spot. She started moving her legs, while her moans got louder and Conan felt she was almost there. He stopped and shushed her before covering her mouth. He he positioned himself in such way that she could feel his hard cock against her thigh. With his free hand, he went down on her, playing with her lips and her clit with two fingers, before putting them in. Good God, she was tight. He bit his lip thinking how tight she would feel against his cock. As he predicted, she moaned louder and he smirked at it. She rocked her hips, she wanted his fingers deeper inside.

He started to finger her faster, and she started to moan louder, muffled sounds coming from her mouth. She had one of her hands against his chest and the other one gripping the arm of the couch. She was breathing hard against his hand and she didn’t want him to stop. He felt her tightening and she came, squeaky moans coming from her mouth, his hand still over her. He observed as her chest moved frenetically, and the sweat that started to drip down her forehead. He slowly took his hand from her mouth and he could still hear a couple of breathy moans coming from her.

“Conan!” he heard a voice call. “Ten minutes!”

He smiled at her and got up. She smiled shyly, looking at the ground and sat up straight.

“Sorry about the ‘old man’ thing.” she laughed, still breathing hard.

He shook his head playfully. “Okay.”

“How do you plan to lose that, boss?” Lily said, picking up her panties off the floor.

“Lose what?”

She sat straight, looked at his crotch and cocked her head. “That boner.”

It could be seen from far away, the outline of a very, very hard dick. Conan touched it.

“It will be gone before I go in.” he purred. “Don’t worry about that.”

He left a little after that, simply running his hand through his hair, and she hated the fact that she had messed it up but he knew how to put it in place like it was never touched during an unprecedented fuck. She put her panties back on and waited for a bit, before going out to watch him. Everything seemed pretty normal and she laughed, not at his jokes, but at the fact that same man now going though monologue jokes fucked the shit out of her a few moments prior. She just couldn’t believe how he held himself up after that.

After going home and taking a good shower, Lily started to think if fucking Conan like that would better his temper. Guy needed sex and she noticed it. It would make her life at work better, until Sona came back that is. She wondered if they could make a deal… everybody would win. She knew it was wrong, but again, all wrong things had been done before. He was apparently great at it, she hated to admit it, but the son of a bitch could make someone cum in a heartbeat. She smirked at herself. She would talk to him the next day.


	6. Chapter 6

Conan drove to work thinking about Lily. Not really about her, but how much he wanted to fuck her. He couldn’t do it while at the office however, and what happened the day prior was just a slip… but he couldn’t resist her for long. He smiled at himself as he parked on the Warner Bros. lot, remembering her face and how she looked when she came right on his fingers and how powerful he felt as she let herself be dominated by her boss on the same couch they used to sit and discuss business on. When he arrived at his office, Lily was already there. Those tight jeans never failed to amuse him, maybe her hotness didn’t have limits and he was still getting used to that.

“Hey, boss?” Lily asked, as soon as Conan stepped in. She was wearing a gray button up shirt.

“Yes?” Conan raised his eyebrows.

“May I talk to you for a second?” Lily looked at him, wearing his brown leather jacket and skinny jeans as usual, looking like a very hot, handsome biker.

Conan walked and sat at his office couch. “Go on.”

Lily crossed her arms. “I know you fucking despise me. I couldn’t give less of a shit about it.”

Conan remained silent.

“But I’m willing to make this work until Sona comes back.”

Conan crossed his legs and put one of his hands on his knee, and placed the other on the couch. “What do you have in mind?”

“Fucking.” Lily said, bluntly. “A lot of it.” Conan smiled.

Conan didn’t really expect Lily to ask him that way, but he planned to let her know he was available. He knew what her intentions were and he had to admire her boldness. Making a move on your boss could always end in contract termination, but the girl knew what she was doing. Conan wondered if she did that before, but it was irrelevant. Both wanted it, and Conan thought the fact she was honest with him on the spot made the situation a lot hotter.

“I believe we think alike.” He nodded.

“Are you free tomorrow?” she asked.

“I’m free now.”

Lily smirked. “Yeah, and I’m sure I don’t want an audience for that.”

“Yeah, I’m free tomorrow. Just give me your address. I’ll be there at ten.”

“I have roommates, Coco.” Lily said.

“You’re coming to my place, lady.” Conan smiled cheekily. “There’s some stuff I need to introduce you to.”

Lily threw her head back slightly, giggling. She wrote her address on a piece of paper and gave it to him. She had given this situation a bit of thought the day prior: the worse that could happen is the man having a poop-piss fetish or something weird like it. She observed him for a bit before the proposal and he seemed good enough. Nothing out of the ordinary. He was good looking, fit, he smelled amazing. Now she wondered if his cock worked as much as his fingers.

Conan knew the risks of accepting a deal like this. That’s what it was, a deal. No feelings involved, at least not from his part. He’d never been so aroused by making someone orgasm like that. He wanted to feel that again. Conan and Lily worked a full day on Fridays, but Conan didn’t tape a show, maybe he would tape remotes or other segments for future shows, but not a taping. They went on with their day normally, sometimes glancing at each other when alone. Conan was in as long as Lily didn’t tell anyone what would happen between them. He wasn’t that big of a celebrity to be followed… he just wanted a good time.

-

“You what? Ew!” Sona exclaimed through the phone.

“Well, I could always leave.” Lily shrugged.

“I wish you’d left, Lilita. Fucking Conan? How...”

“We are both attracted to each other and he needs it… besides, he got better after...”

“After what?” Sona said, startled.

“Never mind.”

“Oh my God, you already did it, didn’t you?” Lily could hear Sona’s disgust over the phone.

“He’s kinda hot and I couldn’t resist it. Yeah.”

“Really?” Sona was shocked at this point. “At the office?”

“Yeah.” Lily rolled her eyes. “But don’t worry. I’ll be fine.”

“I hope so.”

“What do you mean?”

Sona sighed. “See… Conan isn’t in a good place at the moment. He’s sensitive about the show. I don’t think getting involved with him is a great idea.”

“I’m not really gonna get involved, Sona… it’s just for a while. Don’t worry okay?”

Sona agreed. “I hope you know what you’re doing, sis.”


	7. Chapter 7

Conan didn’t know how he would dress up for the occasion. Suit? Just his jacket and jeans? Would he have to wear a tie? He shook his head as he left the shower. He shouldn’t worry that much, should he? Fuck it. Suit, it is. No tie. Good. Conan wondered if going out in a suit was too much, Lily could come out just wearing jeans and a shirt, the way she used to dress up to go to work. He could make a fool of himself. But it didn’t matter. He was planning to order dinner, the house was clean. He had nothing to worry about. Was that… a date? Conan hadn’t had a date in years. That would be fun.

Lily wondered the same thing as she put on a red dress and black wedge heels. Well, she wouldn’t dress up for nothing. If he chose to wear what he wore to work before he taped, that was his loss. She had straightened her hair and curled the strands at the bottom. They would have sex, sure, she would sweat, sure, but that was an effort she was willing to make. Medium sized golden hoop earrings, red lipstick. Yeah, she was ready. And hungry. She hoped he had something to eat.

Conan drove to her building, and called Lily. She grabbed her purse and came down a minute later, and he was relieved about his own choice of clothes. She looked amazing, and if this was a date, fuck it. The cleavage she was sporting was already too much. She quickly entered his car and he drove off.

“I thought you would pick me up in your famous Ford Taurus.” Lily said.

Conan chuckled. “Too recognizable. I thought about doing it though.”

“Conan, you’re driving a BMW with clear windows. If you didn’t want anyone to know about this you’re in bad luck.”

Conan had to nod at that. He tried to seem cool, but her perfume was driving him crazy. Every day, every time he looked at her. He thought she couldn’t be more beautiful. Both tried to keep it cool. Lily noticed his car smelled like him as soon as she entered. She blushed a bit, and hoped he wouldn’t noticed. They barely looked or flirted with each other on the way to Conan’s house, perhaps because they could be seen, and it would be a long story to explain at work.

As they arrived, Conan opened the door to her, since his neighborhood was mostly safe of nosy people. He had a very big beautiful house, with a huge backyard and a pool… for someone who lived alone. She was the first one to enter and he came in right after, admiring her legs and butt as she looked around his living room.

“You hungry?” he purred as he reached her back and placed a kiss on her neck from behind.

“Yup.” She said, as his hands caressed her arms. “You read my mind.”

“Your face too.” He chuckled. “What do you want?”

“Anything but spicy food, of course.” She said.

“Why not…” Conan started to ask, before realizing why.

She laughed. “Just order some chicken, boss. But avoid the spicy sauces.”

-

“I can’t believe we are all dressed up eating chicken.” Conan giggled.

“It’s your fault for not knowing how to cook.” Lily smirked.

“Oh, and how do you know that?”

Lily shrugged playfully. “Sona told me.”

“Damn, Sona!” Conan laughed. “I miss her.”

Conan realized he had more in common with Lily than he thought. She was beautiful, but also very intelligent and endearing, and now he understood how she was so efficient at what she did. It didn’t matter if they were eating chicken and fries as dinner, the conversation was the best part of that moment. Lily asked Conan if he had red wine, he did, and he didn’t oppose himself to drink it while they were having dinner. He had to admit it was good to have company on this giant house of his. Conan told her about his siblings and potato fights and how his mom sometimes got their names wrong as they ran around the house and she was trying to call them out.

Lily told Conan about her childhood, and playing soccer in the middle of the street with an old, deflated soccer ball, as they tried to avoid being hit by a car. Lily told him how she came from Mexico to the United States and for the first time he seemed actually interested on it. She was actually having fun with her boss for the first time since they met. After they finished, Conan showed the house to her, the kitchen – very much unused – made her giggle. She assured him cooking wasn’t that bad. They walked to his office, a lot of books, some guitars and American history paraphernalia. His house looked exactly like she was expecting to.

“So, this stuff is what you wanted to introduce me to?”

“My absolutely square and boring life? Yes.” Conan smiled.

“Oh god, I was sure you had one of those.” Lily pointed to the other side of the room.

She walked to his shelf. “Yes. An Abbey Road vinyl.”

He laughed. “It’s autographed.”

Lily looked at it. “Paul… and Ringo.”

Conan looked at her amused. She handed it back to him. “Not interested.”

He chuckled, a bit confused. “What?”

“Well, I thought that if I didn’t have a great night, I could steal something from you and sell it on eBay.” she laughed.

He raised his eyebrows. “You… could?”

“Yeah, but I would earn more money if the four signed instead of just two.”

He put the vinyl down. “You’re a very mean woman.”

She walked to him and put her arms around his neck. “Next time, I’ll be sure to fuck someone who has that.”


	8. Chapter 8

Lily guided Conan to his bedroom, as she kissed him and held him tight, and he just went with her  flow , no hesitation. They started taking their clothes off as they tripped over themselves at the corridor, first Conan’s jacket, then Lily’s shoes, and she struggled with them, because she didn’t want to let his mouth go. She tasted like red wine, her skin smelled like strawberries, he was so hungry for her it was insane. She took off his button shirt, also struggling with the buttons, even though it was something so easy, she’d never been that horny. She liked the feeling of his soft beard against her cheeks as he kissed her deeply, his hands helping her to get rid of that damn shirt.

They arrived at Conan’s bedroom, his back to the door. They stopped kissing for a moment, and her starving mouth immediately went down to his neck, sucking his sweet, white skin as his hand went caress the back of her head. The other one looked for the doorknob, and opened the door. His room was partially lit, and the windows were open. They could hear the long curtains ruffle as they rushed to Conan’s bed. Lily gently pushed him and sat him at the edge of the bed. She tried to sit on his lap, but he quickly subdued her and laid her down on her back. She giggled as he went to the top, she knew he would end up doing it.

“Not wearing a bra, huh?” Conan purred as he touched her breasts over the fabric of her dress, feeling her very aroused nipples.

“I came prepared.” she whispered.

He proceeded to look for the zipper of her red dress, quickly taking it off and tossing it on the floor. Conan also quickly got rid of his shoes and socks as he kissed Lily. Her red lipstick had faded away to a very fade, pinkish color at that point, similar to the natural color of her lips. She smiled as she heard his shoes fall to the floor and he brought her closer to the center of the bed. She tried to reach his belt buckle when he restrained both of her wrists, stopped kissing her and looked at her with a smirk, shaking his head. She looked playfully pissed and he kissed her again.

He held her down as his mouth gently sucked on her chin, down her neck, her collarbone. His beard tickled her and he went down to her breasts, licking and nibbling her nipples, and she did try to fight his grip, so she could touch his soft, angelic hair, but he was way stronger. His mouth was warm and she had goosebumps every time it touched her skin. She was breathing hard, long sighs coming out of her mouth. She felt his face going down, nuzzling her stomach, licking the spot over her belly button and she just wanted to tug his hair and guide him down to her crotch. He worked slowly, and it was killing her.

His warm hands let her wrists go and her hands went to his soft hair, caressing his scalp as he gently kissed her inner thighs, making her wetter as she waited anxiously for his tongue inside her.  She looked down  to  him, they exchanged brief glances, his eyes darkened by pure lust. He touched her very sensitive clit over the wet fabric of her pink panties. She moaned, as he delayed her pleasure, like a punishment for arousing him every day at the office. 

Lily quivered as Conan took down her panties and positioned himself right in front of her open legs. He bent down, his hands firmly gripping her hips, to eat her up. His tongue tasted her wetness, exploring her pussy lips and her clit, she guided his head as she felt his soft beard gently scratching in between her legs. He teased her, putting his tongue in and out of her, when he felt her body was asking for more than that. His dick was too far to reach and damn, she wanted to suck it.

“Come on, boss.” Lily moaned. “Is that all you got?”

Conan felt dared. He got up, smirked at his aroused lover, before flipping her. She was startled and surprised as Conan put her on fours, and she giggled as she heard him taking his pants off. She couldn’t look, just feel his presence. She was on her elbows and knees, her pussy twitching as he rubbed the tip of his very hard cock against her clit. His free hand caressed her butt as he teased her very wet lips with his shaft. She grunted in response.

“Beg.” he whispered.

“You’re not gonna make me beg.” Lily protested, her head down, a few inches away from the mattress.

Conan approached her from behind, and she could feel his warm body beginning to  rub against her. He grabbed a fist full of her hair and tugged it enough to lift her head up. He approached her left ear.

“I won’t ask you again.”

She could feel his warm body and his cock pressed against her. He was breathing heavily, he wanted it as much as she did. There was no option for her.

“Conan… please.” she whispered. “Please, fuck me.”

Conan obliged with a smirk, thrusting himself in. Lily was sensitive and squeaked as she felt herself being filled all, the way in. Lily felt herself being slapped first on the left butt cheek, then the other. She hated being spanked, and she never asked for it. But  she was so horny and so desperate for cock that she let him do it, every slap felt delicious. She would maybe want to rethink her no spanking policy. His big hands took control of her as he moaned right next to her ear, thrusting himself into her like his life depended on it. She bent down as he fucked her harder and harder, his left hand now playing with her clit, as the right hand still tugged her hair.

“Con-a-a-an!” she moaned and made him smirk for a few seconds, before his face contorted itself again in pleasure. He was almost there.

She moaned out loud, mouth open as his hips collided hard against her butt. Conan eventually let go of her hair and held her hips instead, as she bent and let her cheek grind against the mattress. Conan also had his eyes tight shut, his face pressed against her shoulder. Lily could feel her butt turning red and her knees and elbows warming up as they scuffed against the mattress. The bed creaked as Lily came, Conan felt her tightening and as much as he wanted to hold it a bit more he couldn’t. He cried as he came, filling her with cum as his mind turned into a complete blank, a long, high moan followed by short ones as his voice dropped to a grunt.

Conan slowly removed himself from Lily, she sighed as she felt his cum dripping down her pussy to the mattress. They broke apart and she turned to her back, facing the ceiling. She was guaranteed to be sore the next day, his firm gripping and his spanking doing the job. She looked at him. He was away, but they locked eyes. She observed his face, sweat dripping down his brow, his pompadour was now a mess of wet red hair strands over his forehead. His redness extended all over his body, his chest, down to his stomach and his still half hard cock. He smirked at her after a few seconds.

“Let me know when you’re ready for more.” he said, breathing hard.


	9. Chapter 9

Lily and Conan slept apart. Conan didn’t feel comfortable hugging her, cuddling. That was great sex, he had to say, but that was it. Just great sex. She would probably be gone as soon as he woke up. He fell asleep rather quickly, he was tired. He felt his eyelids closing as his eyes gently glanced at the ceiling. It had been a pleasant night, and he felt satisfied. He slept with his hands placed on his stomach. His bed was so comfortable, but it felt extra comfortable that night. He slept like a rock, and he didn’t recall seeing her move a lot, which apparently meant she was having great sleep.

Conan slowly woke up, his bedroom was naturally lit, but it didn’t bother him. He lazily opened his heavy eyelids and a delicious smell of strawberries invaded him. It was sweet, and deliciously pleasant. As he tried to figure out where that smell came from, his blurred vision finally focused on a bunch of… hair. Very soft hair. His nose was brushing against it. Then he realized he was spooning Lily, his arm around her waist, as she slept peacefully. He didn’t move but felt somehow odd, as he remembered he was far as possible from her when he fell asleep.

He decided not to question it, she just… smelled really lovely, and that’s attractive. He snuggled her neck and she moved a bit, slowly waking up. Lily giggled and opened her eyes, her side to the open windows. She mumbled good morning to him and he chuckled and did the same, both still cuddled for a while, naked bodies pressed against each other. It felt great having someone at home to be close to, for both of them. After a while, Lily got up, and Conan observed as her beautiful figure walked to the bathroom. She was taking her earrings off, she had apparently slept with them on. Her light brown skin looked way more appealing under the sunlight.

She called him from the bathroom, with a very heavy Mexican accent. “Aren’t you gonna join me?”

He giggled, got up and followed her.

-

“You know...” she smiled at him as the water ran down her body. “I don’t think I’ll be clean after this particular shower.”

He smirked. “I think we should start this soon, then.”

Lily brought Conan closer and kissed him, he giggled against her lips and shivered as the very cold water hit his chest and head. He held her waist and her hand went down to his cock and he smiled, as she stroked his half hard cock. She watched his expression changed as she tugged his wet hair, throwing his head back. He let out a slightly high pitched, delicious moan with an open mouth and both giggled, thinking about the night prior in which Conan did the same. She felt him getting bigger and stiffer on her hand.

“God, you get hard pretty fast.” she laughed, staring at his lips.

He smirked as he leaned in to nibble her, and she rubbed the tip of his cock against her wetness. She was ready, so soft and warm. He pressed her back against the glass box and held one of her legs up, around his waist. He kissed her cheek, down to her neck, his wet beard gently rubbing against her skin. She balanced herself by wrapping her arms around his neck. He pushed himself into her, slowly, feeling her walls tightening around the tip and shaft of his hard cock. She moaned louder as he got deeper, pressing their bodies closer together.

He slowly took his dick off, and put it on again as slowly as possible as the water poured down their naked, aroused bodies, her hard nipples pressed against his chest. She looked at him daringly, mildly pissed but aroused and that’s what Conan wanted to see the most. We went deep and she melted, her fingers holding his shoulders so hard she felt she could tore his flesh. He pounded deep and fast, grunting as he projected his body against her. She moaned desperately as she felt every inch of his cock inside of her back and forth and she buried her face on the crook of his neck, begging him not to stop.

He was close when he slip a bit and lost his balance momentarily. Their moans became laughter as they separated and stood back up, fearing he had squished her. They kissed each other, smiling and Conan flipped her, now making sure he would use one of his hands to keep his balance this time. He held her waist as her breasts, her hands, and cheek where pressed against the glass box. Conan stroked his tip against her clit and she smiled, her breath fogging the glass. He put his dick in her tight spot, and his head right next to her neck.

She was so tight and so wet, whimpering at his pounding got faster, and he tried as much as he could to hold it. He felt her tightening, and he knew she was about to come and he placed his fingers sloppily over her swollen clit and massaged it, and a bit after she squirted, her cracking orgasm moan triggering his own, and he moaned out loud next to her ear, taking his dick out and coming all over her lips, clit and inner thighs. They giggled, satisfied and happy as his seed dripped down her legs to the floor. At least they didn’t slip again this time.

“God.” he said, breathless against her neck. “I really wanna fuck your ass.”

She laughed. “Maybe...” she inhaled. “...maybe after breakfast.”

  
  



	10. Chapter 10

“You know...” Conan purred at Lily, smoothly. “I’m liking our little agreement.”

Both were now eating breakfast, some toast, and Conan was eating eggs and bacon. Lily was drinking cocoa, as she didn’t like coffee at all. Coffee didn’t do much for Conan, besides keeping him awake, so he was drinking orange juice. Both smiled at each other, the inhibition that could exist between them was now completely gone, as she wore his blue button shirt and he was wearing nothing but his underwear. They had no idea what time it was, even though Conan’s dining room had large windows and sunlight was coming through them, it could be either nine, or four. It didn’t matter.

“Nice, isn’t it?” she said, with a cheeky smirk.

He checked her out. “Yes.”

“I’m keeping this one.” she said, referring to the shirt she was wearing. She had her partially wet hair in a bun.

“I’m not objecting to that.” he said, drinking his juice. His hair was wet, covering his forehead.

“Tell me.” she said, chewing her last bite of toast. “Why did you agree to any of that?”

Conan sighed in amusement. “Oh, dear Lily...”

She giggled as he paused, to reveal the reason.

“I wanted to fuck you since the first time you entered my office.”

She pouted, his comment wasn’t surprising to her anymore. “How much?”

“Very much. I thought about it a lot.”

“So basically...” she got up and sat on his very welcoming lap. “While you were arguing with me...”

She wrapped herself around him, her hands stroking his wet hair. “…I was thinking of each and every way I wanted you to suck my dick.”

She kissed him as both giggled. He was tasting like orange juice, but his own mouth was so sweet at this point that she felt the need to kiss him over and over again. The fact she smelled like him after using his hair care products and soap didn’t stop him at all. He kissed back, with the same energy he did it before… and before that. Her crotch was grinding against his again, and she noticed him getting progressively harder, and the memory of herself calling him ‘old man’ came to mind, but boy, she was wrong about that.

“Speaking about sucking cock...” he whispered. “...you owe me like… three blowjobs.”

“Just three?” she pressed her lips against her delicious smelling neck. Her hands sloppily stroked his hard shaft. “I was hoping for more.”

He sighed as she kiss ed his chest, her other hand making its way down his body, feeling his warm skin against her palm. She placed soft kisses on his abs, still impressed o n how he maintained such a good physique at that age. He was beyond hard now, so Lily didn’t waste any time and slipped down, to her knees and took his briefs down to his legs. Lily took his cock inside her hot mouth as she looked at her lover, appreciating the sensation of having the tip of his cock sucked, that delicious feeling he hadn’t experienced in a long time.

Lily played with it, swallowing his cock whole, her nose slightly brushing against his skin and his reddish pubes. She took her mouth away completely, slowly, killing him, and then swallowed him again, like a pro and he whimpered at the sensation of his dick being in and out of her mouth. He knew she was edging him, and he was trying very hard not to cum… not yet. But it was difficult. She stared at him with pure lust in her eyes, as his cock twitched, ready for the release. Conan was starting to sweat at that point, his face turning pink, and his lips turning pinker.

She moved on to softly suck the tip of his cock like a lollipop. The motion and her hand stroking his veiny shaft broke him. His moans went from breathy sighs to desperate, loud grunts. He felt like the room was spinning as he came, all over her face, without a warning. He couldn’t speak for a second, and Lily missed some of his cum, swallowing only half of it. The other half hit her left cheek and lips, dripping down her chin. She got up, her knees all red, satisfied as she looked at his face.

His eyes were closed, enjoying the sensation. He sighed with an open mouth and opened his eyes, just in time to check her cleaning up her chin and licking her fingers. He looked so blissfully satisfied. Her knees were red, and Lily herself was red, which made her even hotter. They stared at each other for a second and Conan giggled.

“Two now.” he said softly, almost a whisper.

“Yeah.” she agreed. “Two.”

-

“What’s in your mind?” Conan asked.

“Just how much you hate me, and how powerless you feel next to me at the same time.”

Lily was sitting by Conan’s pool, her legs deep inside the water. She didn’t turn to answer him, and he felt like it was an invitation to come and sit next to her. The sun was setting down. Conan knew he could be photographed at any minute with his assistant wearing his shirt, and himself wearing only black briefs. He didn’t care anymore. It would be a great view. He side hugged her shoulders.

“I know it’s not the first time you fuck your assistant.” Lily poked him. “But I didn’t know that was so frequent.”

“We don’t talk about Lynn in this house.” Conan said. “Besides, I never fucked Sona, so you’re completely wrong.”

Lily laughed. “It’s just because she thinks you’re gross.”

“Do you agree?” he purred next to her ear. Her hair was now loose, and although she she smelled like him, her skin still smelled as delicious as when she came in.

“Nah.” she said as she moved her hand gently up and down his left thigh. “You smell great, actually.”

“You wanna give our neighbors a little show, Lilita?” Conan nibbled her ear.

“Yeah.”


	11. Chapter 11

“Why the beard…?” Lily asked. “Why now?”

Lily gently stroke Conan’s beard. They were strangely close now, bodies and minds. She had her cheek and ear pressed against his bare, warm chest, looking up to his chin as he faced the ceiling. None of them even bother to dress up. They didn’t know what time it was. They ignored the cellphones ringing throughout the day. It was dark and it felt cold enough, the air conditioning was off. They didn’t turn on the lights as it got darker. The sun was gone at that point and all they had was the moonlight.

“The day I lost the Tonight Show...” he said emotionless, in a robotic way, as he tried to disassociate himself from the moment to avoid living it through memory again. “…I said ‘at least I don’t have to shave every day anymore.’ And I kept that mentality for months and here we are.”

Lily remained silent, feeling the vibration of his voice and his heartbeat running through her ear. “I keep reliving that moment, asking myself what I did wrong and what I could do to make it better.”

Lily let her hand fall to his chest. “Nothing, maybe. That’s just how life is.”

Conan sighed. Lily continued. “We fail sometimes, with ourselves, with the world; and people fail with us. You have to live with that now.”

Conan noticed some sort of sadness on her tone of voice. “Did you fail with someone?”

“Maybe.” she said. “But I feel that even if I did everything for him, we would still be a failure as a family.”

“Who...” Conan softly asked.

“My father.” Lily whispered. “I wish we had a better relationship.”

Conan looked down at her soft hair and reached to stroke her head. “Wanna talk about it?”

“No.” she said softly. “I just feel pain.”

Conan held Lily for what it seemed like an eternity. They fell asleep cuddled, in the same position they were talking before. The bed was inviting for sex, of course, but after this little exchange, they felt… safe, and understood. Especially Conan, who got comforted by many people in so many ways, but it never felt as intimate and special as his naked assistant in his house telling him that we have to get over our deceptions. Conan felt so relaxed that drifting to sleep was so much easier than the days he was alone, worrying about all of it. He didn’t know if this was connected to Lily or he was finally reaching the Kubler-Ross stage of acceptance. Either way, something happened. Something positive.

-

Conan and Lily overslept, and by the time they woke up, they had to go to work. They had breakfast together once more and Conan took her home so he could change, since it would be really weird if she went to work wearing a low cut, bright red dress… with no panties. She showered quickly as he waited in the car, and she changed to a t-shirt, skinny jeans and sneakers. Conan smiled as she came to the car. Nothing on her looked ugly, apparently. Just watching her going in wearing a sexy red dress and coming out wearing a t-shirt in itself was already kind of amusing. They tried to play it cool as they arrived to the Warner lot in Burbank. Their conversation during the trip was mostly about work stuff.

The day went on without trouble, Conan seemed more friendly towards Lily, and even when they disagreed, it was handled in a peaceful way. The interns, Andy, Jordan… everyone was extremely surprised, including Jeff. They decided to take it as Conan realizing how much of a dick he is, and trying to make things better with her. It made the environment feel so much lighter. At the end of the day, Lily was ready to take the subway, when Andy offered her a ride. She decided to take it.

“Lily...” Andy said, as he drove her home. “You’re fucking Conan, right?”

Lily’s heart almost stopped. She stared at Andy as they stopped at a stop sign and he adjusted his glasses.

“I...”

“I’ve heard the two of you… that day? Mike almost caught you two.”

“Andy, I’m just...”

Andy shook his head in concern, looking at the road as he drove. “Conan has been my friend for almost twenty years now, Lily. I know stuff.”

“Yeah, we are, but...”

“You know what you’re doing, yes.” Andy interrupted. “You’re both adults.”

Lily looked confused. “But listen to me, Liliana. Conan isn’t in a good place right now. He might hurt you.”

Lily wanted to sound as confident as she could, but she ended up sounding insecure. “It was just a friends with benefits thing. He’s happy, therefore I am happy.”

Andy parked in front of her apartment. “But he isn’t really your friend, is he?”

Lily shook her head. “I appreciate the concern, Andy. I’m gonna be fine.”

Andy shook his head. “I hope so.”


	12. Chapter 12

Lily thought about what Andy had said. If he knew, maybe more people at work did. She didn’t know what concerned her more, the possible fame of the whore who’s sleeping around with the boss, or the fact that her sexual life wasn’t that private anymore. She hoped that they only noticed their body language towards each other, not… Conan getting his dick wet at his office. The way Andy talked about her feelings affected her, because she was slowly realizing she liked Conan beyond all the sex they had. But she dismissed it as a little crush on a good looking man. It would pass eventually.

The next day, Conan told Lily he had a surprise for her. She was… shocked at first, and he didn’t reveal what it was. She worked through the day thinking about it, and it ended up making her a little nervous. Conan eventually asked her to go out and get his lunch. As she walked around the Warner lot, she heard a familiar voice calling her name. She froze, like every bone and muscle inside her body turned to heavy stone. She took what seemed like forever to turn to him.

“¿Papá?”

Lily’s father was a small man. Small, but dangerous. He had evil in his eyes. Lily hadn’t seen him in years, but she felt unpleasant goosebumps as he came closer. She wanted to run, but she was too scared to do so. She was taller than him, but as he approached she started to shrink as if his figure of authority made her feel insignificant. Conan came to talk to Lily about his lunch, as he was starving and saw the weird exchange. He decided to get closer to them.

“So, that’s what you’re doing? You’re here in Los Angeles living your best life while I’m back in Mexico with nothing?” 

Lily shook her head, as tears started streaming down her face. “You’re terrible, useless, like your mother.”

The man was now screaming. “How did you get this job? Whoring around? Who did you fuck? Did you even think that your father could use some help?”

Lily started to go back, slowly, as the man confronted her, diverting the attention all to them. “Where’s your mother? That absolute cunt! You snakes, you all!”

Conan arrived in time to intervene. “Mr.  Peregrín , I’m afraid you have to leave.”

The man didn’t back off, even Conan’s height didn’t scare him at all. “I’ll take this cheap whore with me.”

“I’m gonna call security on you.” Conan stood between father and daughter, shielding her from anything that her father could do.

“Why are you defending this lowlife, shitty Mexican puta, are you fucking her too?”

Conan lost his patience. “If you call her a whore once again...” he mumbled, gently shaking his head. “I’ll break every fucking bone of your body.”

Conan clenched his fists tight and before he could act, security came and took the man away. He accompanied them and made sure that the man was escorted out of the building. After that, he looked around for Lily and she wasn’t there anymore. He was hungry, but he ran around the lot looking for her, and found her at his office, sitting on the floor and hugging her legs. She was crying uncontrollably, like she’d seen something so upsetting that caused her mind to break. She was absolutely oblivious to his presence, sobbing loudly and desperately. Conan didn’t know what to do. He stared at her for a while, until she slowly looked at him.

She had puffy eyes, and she looked extremely scared. Conan didn’t really know how to act, and approached her carefully. She was shaking. He wanted to give her a hug, but he didn’t know if she wanted one. He sat on the floor beside her, as she got quieter, her sobs going away. She took some deep breaths, as she realized her threat was probably far away at that point. Conan saw that calling her father was a mistake and maybe that was the reason why she didn’t want to talk about him in the first place.

“My dad...” she said, looking at the floor, as if she owed him an explanation. “My dad is not a good person.”

Conan looked concerned. “He’s a drug dealer for a Sinaloa cartel.”

She paused, reliving her memories after swearing she was past them. “We lived in constant fear of being killed, because he would make deals he couldn’t pay, he owed money to people and they came to our house multiple times to collect money.”

Her lips were trembling. “We’re lucky we ain’t dead.”

Conan regretted calling her father  more and more . She continued. “He hates me because I was the one who made my mom’s mind to leave him. I had a little baby brother, and I didn’t want him to remember what is like...”

She frowned, out of fear or what could be described as pure indignation. “...what is like to have a gun to your head.”

She looked at him finally. “I don’t know how he found me...” her voice cracked. “...but I can’t go home alone tonight. I may have to move.”

Conan nodded. He looked at her, he wanted to risk a hug but… this entire thing was his fault in the end. He felt like he needed to, but he didn’t have the courage to tell Lily that he was the one who called her father. He thought that maybe seeing her father would make her happier, but he clearly didn’t know that what she wanted was a father figure, a good role model who could be there for her when she needed him to. He had to admit, his childhood and early life was considerably better than most people’s and he never knew what this was like. The man seemed calm and collected on the phone, as if he’d love to see his daughter again. Terrible idea.

Conan made sure to call the police, that man probably had some warrants or something against him, and Conan wanted him to be behind bars as soon as possible. The look of evil in his eyes said too much: he’d seen a lot and he’d done a lot too. Conan didn’t want Lily to be another one of his casualties. Lily didn’t explain much further, but she confirmed that her dad’s ordeal involved death, and she feared for her life ever since she was seven, the age she realized her dad didn’t have a normal job. They ran away when she was ten, and she never looked back.


	13. Chapter 13

Conan and Andy made an agreement to pick Lily up and take her home for a few weeks. Lily insisted they shouldn’t have to do this forever. Deep inside, she feared for both of their lives. None of them gave up, they cared about her and wanted to make sure she was safe. Lily would look up for any news that her father was going to jail. She knew that wishing that upon her father wasn’t the best thing, but if he hurt others the way he traumatized her, then maybe prison was his rightful place. Andy didn’t mention Conan and Lily sleeping together again after this, and they eventually stopped doing it. She wasn’t on a place to do it at that moment. She knew that her father liked to call her names to insult her, but sleeping with the boss isn’t exactly what she wanted to be known for, although ‘daughter of a criminal’ wasn’t a better choice.

Lily however, started to wonder how her father had found her. She was always running away from him, and her mother, although still in Mexico, was far away from him as well. It had been ten years without any signs of him being alive, and Lily thought he was long gone. Now, she knew he was out there. But who brought him in… who had the power to locate him and tell him where she was working? She doesn’t remember mentioning his existence to anyone except…

Conan?

“How many fucking times are those acts gonna cancel on me?”

“You should cover it with the band.” Lily replied.

His face was turning red. “What a ridiculous idea.”

Lily frowned. “I could call any other band...”

“Where, Liliana? Where? Where the fuck are we gonna find a band who will be able to be here in less than two hours?”

Lily shrugged. “I don’t know, but I’ll try.”

Conan shook his head. “Just talk to the booker, you should take care of it.”

“I will. But if you were nicer about it...”

“Well, if everybody here did their job I wouldn’t have...”

Lily got closer to him, the same way she did the first time they had a fight. “Listen.” she said, pointing her finger against his chest once more. “You don’t have to talk to me like I’m an idiot. I know you are referring to me.”

Conan rolled his eyes. She smelled so good it was difficult to actually keep an angry face. “Second, that’s not my fucking job. I’m not your booker, and I told you several times. If you’re gonna be an asshole, I may bring her here, because I noticed that you only have a problem with me, of all people.”

“Only because…”

“Because nothing, O’Brien!” she exclaimed, her hot, Mexican accent coming through. “Andy was right after all.”

Conan started to get pissed off. “Andy? What did Andy tell you?”

Lily sighed. She knew she had crossed the line. “Nothing that concerns you.”

“Tell me.” His hotness peeked when he was annoyed.

Lily rolled her eyes. “He said you’re not my friend. And I can see that now.”

Conan raised his eyebrows. “Oh, so at one point you thought you were my friend? You work for me, Lily. I’m your boss and that’s it.”

“He also said that fucking you would lead me nowhere. He was also right about that.”

Conan chuckled. “But the way you moaned my name for hours just shows how much you wanted it.”

Lily grunted and left the room. Conan went back to research on his guests for the taping. He couldn’t concentrate about how annoying he was. He was annoyed at the fact that someone else knew he and Lily slept together, but most of all, he was annoyed at Andy interfering on personal business. He ended up going to Andy’s office, to talk about it. Andy was sitting at his computer, when an angry Conan entered and shut the door loudly. Andy already had an idea of what he would say.

“Lily and I fucking is none of your business, Andy.” Conan frowned at him, without even a greeting.

“It affects us at work, Conan.” Andy was honest. “Everybody knows you guys hate each other, and still I walked on you two fucking. More than once.”

“It has nothing to do with anyone...”

“It is when you’re fingering your assistant over your desk with an unlocked door. To be honest, it shouldn’t even happen here!”

Conan grunted. Andy continued. “I really like Lily, Conan. She’s really nice and hardworking. But I realized all you do is push her away, even  when she’s trying to help.”

“It’s just sex.”

“I came to realize she really likes you.” Andy shook his head. “You’re just playing with her.”

Conan left Andy’s office feeling a bit guilty. As much as he denied, Lily was special to him too. But it was just sex, and he could just have sex with someone else. She would leave soon, hopefully and Conan never wanted to see her again after this. He could try the cue card girl, or the wardrobe girl. Some other girl. But no, not Lily. Lily should be… gone. Sona would be back, as grumpy as she always was, and everything would be back to normal. Or so he thought.


	14. Chapter 14

Conan had started acting weird after a while. He started to distance himself from Lily after  his conversation with Andy . They were never close, but he was even more distant, even when they fought constantly, he never looked… so disassociated. Not from work, but from her. He wasn’t hostile, he wasn’t mean. He just existed next to her, he asked her the basic, and didn’t look at her in the eyes for long, which was uncharacteristic of someone extroverted like he was. This went on for a couple of weeks after Lily’s dad appeared there. Lily didn’t want to talk about it, and he never mentioned it either.

Lily started to consider again what Andy had said. Clearly, Conan wanted nothing to do with Lily after their fling, and her plan had failed miserably. Lily couldn’t shake up the feeling that Conan did something. And she needed to know what it was. He referred to some ‘surprise’ before her dad showed up and Lily hoped that encounter wasn’t the surprise. That would be distasteful. Andy’s voice popped up inside her head, repeating what she had heard from him the day he gave her a ride. ‘He’s not really your friend, is he?’ and Lily started to put the pieces of it together. She stormed into his office as he was reading and revising some monologue jokes.

“Conan?” she was loud, indignation and rage found on her voice tone. “Did you call my father?”

Conan looked up, and realized how angry she looked. Before he could answer, she continued. “Why did you think this was a good idea?”

“I thought you wanted to see him.” Conan said, calmly.

“I just said I wished I had a good dad, not ‘hey, call my psycho dad for a meeting’!” her face was all red at that point.

Conan frowned. “I was just trying to make you happy.”

“By looking up my stuff and my past and bringing up a person who I clearly didn’t want to talk about!?”

“You never mentioned he’s dangerous. I would never know.” Conan looked back at his papers.

Lily seemed distressed. “Couldn’t you just stand me like a normal person? I never did anything against you!”

Conan continued silent as Lily vented. “Ever since I got here, all you did was being unpleasant. I don’t think you ever worried about someone who isn’t yourself!”

Everybody in their vicinity could hear Lily’s loud voice. Sona had just arrived at Warner, to talk to Conan about some stuff and to check on Lily. When she entered the office she witnessed Lily aggressively arguing with Conan, and Conan didn’t seem to give a shit. Sona already knew, based on Lily’s calls, that they didn’t get along pretty well. But she had no idea what they were arguing about this time. She was so surprised that she didn’t interrupt them.

“Why would you want me to be happy? You never cared about me before!” her voice was getting louder.

“Like you can’t get over the Tonight Show? It’s not my problem. It’s done, Conan. You lost it!”

“You’re fired.” Conan said, calmly.

“What?” Lily said

“Go to human resources, I don’t want to see you here by four.”

Lily looked at him, surprised. She never thought Conan would actually fire her for something so petty. She knew  Sona was back , and maybe that was the reason. Unfortunately, as it seemed, Lily started liking him after being together. She tried not to, but she saw he wasn’t just a jerk and underneath all of that suffering and bitterness, there was just… a broken man, who needed to be understood and comforted. But it wasn’t her job to do it. She had done her job, and the six months expired. She  looked at Sona and shook her head, trying to hold back her tears. She had failed.

The tears started to stream down her face as she left the room, a heavy silence followed. Sona looked at Conan, who continued reading his monologue jokes like nothing had happened. She approached his desk… carefully.

“What was that?”

“What was what?” Conan replied, not looking up. 

Jeff Ross entered the room, about being alerted there was a commotion. “Conan, we agreed we wouldn’t fire...”

“She disrespected me. She had to go.”

“What did you do to her, Conan? I know she wouldn’t explode over you.”

“She said she wanted to be closer to her dad, so I called him, but I didn’t know he was a dangerous criminal that could maybe kill her.” Conan said, casually.

Sona shook her head in disbelief. “You know this is against company privacy...” Jeff said.

“I own the company.” He looked up, his stoic expression was both amusing and scary.

“You didn’t have to do that to her, even though you didn’t like her, she was a good...” Sona said.

“You’re back, I have no reason to keep her.” Conan said, now looking at Sona. “She has to go. I don’t want to see her ever again.”

“Why?”

Conan sighed, showing emotion for the first time that day. “Because I’m madly in love with her.”


	15. Chapter 15

**Notes for the Chapter:**

> Hi folks I’m back, cause bitch doesn’t die.

Sona stared at Conan silently, for a minute, that felt like ten years. She expected any other answer, but this one. She didn’t know what happened between them exactly, except for the fact they were sleeping together. Sona told Lily Conan was broken and that he felt like shit after all that happened and after losing the Tonight Show. But her friend insisted, and said things got better as soon as they started sleeping together. Judging by Conan’s state, that’s probably not what happened. Jeff was called and had to leave the room. He asked Sona to try and talk to Conan about it.

“You could’ve just…” Sona paused, thinking about how absurd all of it was. “You should’ve talked to her.”

“And say what?” Conan said back, trying not to look at Sona’s eyes, fiddling with papers. “I would give her hope, Sona. She would try to stay and fix me.”

His voice cracked. “I’m a broken man. I can’t be fixed.”

Sona approached his desk, trying to comfort him, but he stopped her.

“Listen…” he said, now looking at her in the eyes. He looked broken, indeed. “I know we have a show in a few hours, but could you … kindly leave me for a moment?”

Sona sighed. “Yeah. I will do that. But if you need anything, just text me, okay?”

“Yeah. Welcome back.”

Sona left the office and closed the door behind her. Conan looked up, throwing his head up to face the ceiling, to avoid any tears to come out. He held himself as much as he could in front of his assistant, like he always did when he had problems. The Irish way. He pretended nothing was happening, and went on. But now he wasn’t so sure he could go on. As soon as the reality hit him, that he had the possibility of never seeing Lily again, as soon as he realized it… he started to cry uncontrollably. He sobbed, silently at his office, surrounded by artwork of himself, smiling happily. It felt like he was having a nightmare at a haunted house.

Conan closed his eyes, but even in the position he was, he couldn’t stop the tears from coming. He was a mess emotionally, so he just let it happen. He would never feel her lips against his again. The smell of strawberries, the softness of her hair, the warmth of her chocolate brown eyes. It was all gone. He would hurt her. He hurt himself almost every day with thoughts, the thoughts of not being good enough, not being deserving of what he conquered. The thoughts of being a dumb, a fool. He didn’t want to bring her to this world. The truth was that he didn’t consider himself good enough for her, and there was no other way of explaining this.

-

Lily threw her badge on the floor, crying, and ran from Warner Bros. Studios Burbank to never come back. She would never work at the industry again, she would never see Conan again. People saw her and tried to stop her, but she wanted to leave that goddamn place and forget what happened in the last six months. Six months… that went by so fast and caused so much damage to her heart. If she knew… if she only knew. Lily now blamed herself for it, proposing sex to Conan was the worst thing she’s ever did. Now she was tied to him – a man who didn’t love her. But she saw clarity through the mess. He was extremely broken, but he was only human. He could be sensitive, he could be… a decent man.

But every chance they had to be together was blown away. What was she thinking? That he would magically fall for her? Conan never liked Lily and he made sure she knew that. Her heart saw something different than that. When she looked into his sky blue eyes, she saw something. A different, soft look. He never said anything about it. She felt like she could understand him after being intimate with him so many times. She was wrong and now her heart was troubled. Turns out her feelings for him were stronger than she thought. She wanted to be in his arms more than anything in this world…

Lily decided to leave the United States for her home country of Mexico. Fuck her working visa. She didn’t want to hear a word in English anymore. She didn’t want to be in the city of angels, suffering like she was in hell. She took the subway home and packed up her stuff. She had some missed calls, some from Andy, Sona, and even Jeff sent her a message. If she needed to go back to finalize anything about her firing, she wouldn’t. Fuck that. Fuck everything. She was hurt and angry, crying uncontrollably. He would never hurt her again after that. No one would. She left that night, feeling like every drop of water inside her body was made into tears rolling down her cheeks. That studio wasn’t her place to be. Neither his heart.


End file.
